5-Chloro-8-hydroxyquinoline → HCID 15274186, compound

HRID 1025535Notes

Reaction equation

HRID 1025535 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[OH-].[Na+].[CH2:15](Br)[CH:16]=[CH2:17]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC=CC=1>[CH2:17]([O:12][C:9]1[CH:10]=[CH:11][C:2]([Cl:1])=[C:3]2[C:8]=1[N:7]=[CH:6][CH:5]=[CH:4]2)[CH:16]=[CH2:15]

Participants

6

Reactant 3

HCID 28175-Chloro-8-hydroxyquinolineHCID 7841Allyl bromideHCID 14798Sodium Hydroxide

Product 1

HCID 15274186HCID 15274186, compoundYield 77.4%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 241BenzeneSolvent

Procedure

A solution of 5-chloro-8-hydroxyquinoline (1 mmol, 180 mg) in aqueous NaOH (0.25 M, 8 mL; 2 mmol) containing tetrabutylammonium bromide as the phase-transfer catalyst (0.1 mmol, 33 mg) was stirred for 30 min., and allyl bromide (1 mmol, 85 μL) and benzene (8 mL) were added and the reaction mixture was stirred vigorously at 50° C. for 14 h. The reaction mixture was partitioned between water (15 mL) and EtOAc (15 mL) after cooling to room temperature and the extraction was repeated twice. The organic layers were combined and washed with 1 M NaOH solution (15 mL) and concentrated. The crude product was purified by flash-column chromatography over silica gel using 1:2 hexanes-ether as eluent to afford quinoline 3a as a light-brown solid (170 mg, 64%).

Workup

  1. stirringthe reaction mixture was stirred vigorously at 50° C. for 14 h
  2. customThe reaction mixture was partitioned between water (15 mL) and EtOAc (15 mL)
  3. extractionthe extraction
  4. washwashed with 1 M NaOH solution (15 mL)
  5. concentrationconcentrated
  6. customThe crude product was purified by flash-column chromatography over silica gel using 1:2 hexanes-ether as eluent

Sources & evidence

ORD record
ord-0d67a59054c34cdebc98c2d61b42cd28
Source dataset
uspto-grants-2014_05
Patent number
US08729097B2

Reaction notes

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